Spektraris NMR
Taxol B
Common Name: Taxol B
Synonyms: Cephalomannine
CAS Registry Number: 71610-00-9
InChI: InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
InChIKey: InChIKey=DBXFAPJCZABTDR-WBYYIXQISA-N
Formula: C45H53N1O14
Molecular Weight: 831.9
Exact Mass: 831.3466
NMR Solvent: CDCl3
MHz: 400.0
Calibration: TMS
NMR references: Sénilh, V., Blechert, S., Colin, M., Guénard, D., Picot, F., Potier, P., and Varenne, P. (1984). Mise en Évidence de Nouveaux Analogues du Taxol Extraits de Taxus baccata. J. Nat. Prod. 47, 131–137.
Chmurny, G.N., Hilton, B.D., Brobst, S., Look, S.A., Witherup, K.M., and Beutler, J.A. (1992). 1H- and 13C-nmr Assignments for Taxol, 7-epi-Taxol, and Cephalomannine. J. Nat. Prod. 55, 414–423.
Species: Taxus
Notes: This compound was also identified by Miller, R.W., Powell, R.G., Smith, C.R., Arnold, E., and Clardy, J. (1981). Antileukemic alkaloids from Taxus wallichiana Zucc. J. Org. Chem. 46, 1469–1474 however Senilh et al., had more complete proton NMR data. 13C-NMR Chmurny et al., 1992 has 13C nmr data.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.66 | d | 7 |
| 3 | 3.75 | d | 7 |
| 5 | 4.92 | dd | 7, 2 |
| 6 | 1.85 | m | |
| 6 | 2.5 | m | |
| 7 | 4.4 | m | |
| 10 | 6.25 | s | |
| 13 | 6.18 | t | 9 |
| 14 | 2.22 | m | |
| 16 | 1.25 | s | |
| 17 | 1.12 | s | |
| 18 | 1.81 | s | |
| 19 | 1.67 | s | |
| 20 | 4.18 | d | 8 |
| 20 | 4.29 | d | 8 |
| OAc | 2.24 | ||
| OAc | 2.36 | ||
| 2' | 4.7 | d | 3 |
| 3' | 5.76 | dd | 9, 3 |
| 3' Ph | 7.36 | ||
| NH | 6.5 | d | 9 |
| OBz | 7.46 | m | |
| OBz | 8.05 | dd | 8, 2 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 79 |
| 2 | 74.9 |
| 3 | 45.5 |
| 4 | 81.1 |
| 5 | 84.4 |
| 6 | 35.5 |
| 7 | 72.17 |
| 8 | 58.5 |
| 9 | 203.8 |
| 10 | 75.6 |
| 11 | 133.1 |
| 12 | 142.2 |
| 13 | 72.24 |
| 14 | 35.5 |
| 15 | 43.1 |
| 16 | 21.8 |
| 17 | 26.8 |
| 18 | 14.7 |
| 19 | 9.5 |
| 20 | 76.5 |
| 4-OAc C=O | 170.4 |
| 4-OAc CH3 | 22.5 |
| 10-OAc C=O | 171.4 |
| 10-OAc CH3 | 20.8 |
| C=O Ph1 | 167.1 |
| q-Ph 1 | 129.15 |
| o-Ph 1 | 130.3 |
| m-Ph 1 | 128.3 |
| p-Ph 1 | 133.8 |
| q-Ph 2 | 131.3 |
| o-Ph 2 | 127 |
| m-Ph 2 | 128.8 |
| p-Ph 2 | 129.03 |
| 5' | 169.1 |
| 6' | 138.2 |
| 7' | 132 |
| 8' | 13.9 |
| 6' CH3 | 12.3 |
